![[(difluoromethyl)thio]methylbenzene](/Databaselist/images/loading.webp)
1512-30-7Relevant academic research and scientific papers
Photoredox-Catalyzed Intramolecular Difluoromethylation of N-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones
Zhang, Zuxiao,Tang, Xiao-Jun,Dolbier, William R.
, p. 1048 - 1051 (2016)
A visible light-mediated difluoromethylation of N-benzylacrylamides with HCF2SO2Cl as the HCF2 radical precursor is described. The reaction incorporates a tandem cyclization/dearomatization process to afford various difluoromethylated 2-azaspiro[4.5]deca-6,9-diene-3,8-diones bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields.
Efficient cu-catalyzed atom transfer radical addition reactions of fluoroalkylsulfonyl chlorides with electron-deficient alkenes induced by visible light
Tang, Xiao-Jun,Dolbier, William R.
supporting information, p. 4246 - 4249 (2015/04/14)
Fluoroalkylsulfonyl chlorides, RfSO2Cl, in which Rf=CF3, C4F9, CF2H, CH2F, and CH2CF3, are used as a source of fluorinated radicals to add fluoroalkyl groups to electron-deficient, unsaturated carbonyl compounds. Photochemical conditions, using Cu mediation, are used to produce the respective α-chloro-β-fluoroalkylcarbonyl products in excellent yields through an atom transfer radical addition (ATRA) process. Facile nucleophilic replacement of the α-chloro substituent is shown to lead to further diverse functionalization of the products.
Photoredox-Catalyzed Tandem Insertion/Cyclization Reactions of Difluoromethyl and 1,1-Difluoroalkyl Radicals with Biphenyl Isocyanides
Zhang, Zuxiao,Tang, Xiaojun,Dolbier, William R.
supporting information, p. 4401 - 4403 (2015/09/28)
Using visible-light photoredox conditions, difluoromethylation and 1,1-difluoroalkylation of biphenyl isocyanides have allowed the synthesis of a series of 6-(difluoromethyl)- and 6-(1,1-difluoroalkyl)phenanthridines via tandem addition/cyclization/oxidation processes. The reactions are carried out in wet dioxane at room temperature using fac-Ir(ppy)3 as catalyst to form a large variety of substituted phenanthridine products in good to excellent yield.
Direct Photoredox-Catalyzed Reductive Difluoromethylation of Electron-Deficient Alkenes
Tang, Xiao-Jun,Zhang, Zuxiao,Dolbier, William R.
supporting information, p. 18961 - 18965 (2016/01/26)
Photoredox-catalyzed reductive difluoromethylation of electron-deficient alkenes was achieved in one step under tin-free, mild and neutral conditions. This protocol affords a facile method to introduce RCF2 (R=H, Ph, Me, and CH2N3) groups at sites β to electron-withdrawing groups. It was found that TTMS (tris(trimethylsilyl)silane) served nicely as both the H-atom donor and the electron donor in the catalytic cycle. Experimental and DFT computational results provided evidence that RCF2 (R=H, Ph, Me) radicals are nucleophilic in nature.
Photoredox-catalyzed tandem radical cyclization of N-arylacrylamides: General methods to construct fluorinated 3,3-disubstituted 2-oxindoles using fluoroalkylsulfonyl chlorides
Tang, Xiao-Jun,Thomoson, Charles S.,Dolbier, William R.
supporting information, p. 4594 - 4597 (2015/01/08)
Fluorinated radicals were generated from RfSO2Cl by photoredox catalysis under mild conditions, where Rf = n-C4F9, CF3, CF2H, CH2F, CH2CF3, and CF2CO2Me. This method provided a general way to construct fluorinated 2-oxindoles from reaction with N-arylacrylamides via a proposed tandem radical cyclization process.
Process for the synthesis of hydrogenofluoromethylenesulphonyl radical derivatives
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Page/Page column 5, (2008/06/13)
The invention concerns a method for synthesis of hydrogenofluoromethylenesulphonyl radical derivatives, comprising: a) a step which consists in condensing a thiolate (that is a monoalkyl sulphide salt) with a compound having a sp; 3hybridized carbon bearing a hydrogen, a fluorine, a heavy halogen selected among chlorine, bromine and iodine and an electron-attracting group selected among fluorine and those whereof the is not less than 0.2, advantageously than 0.4; b) a step which consists in oxidizing the compound obtained in step a). The invention is applicable to the synthesis of various compounds having a suphinyl or sulphonyl group.
A new synthesis of difluoromethanesulfonamides - A novel pharmacophore for carbonic anhydrase inhibition
Boyle, Nicholas A.,Chegwidden, W. Richard,Blackburn, G. Michael
, p. 222 - 224 (2007/10/03)
Preparation of the key intermediate carboxydifluoromethanesulfonamide provides direct synthetic access to a wide range of novel difluoromethanesulfonamides, including the acetazolamide analogue (2-ethanoylamino-1,3,4-thiadiazol-5-yl)-difluoromethanesulfonamide. Their water solubility and stability, ether partition coefficient, pK, and submicromolar dissociation constants for human carbonic anhydrase isozyme II (HCA II) make them promising candidates for topical glaucoma therapy.
METHOD FOR PRODUCING BENZYL(DIFLUOROMETHYL) SULFIDE COMPOUND
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Page/Page column 9, (2010/02/11)
PROBLEM TO BE SOLVED: To provide a method for producing a benzyl(difluoromethyl) sulfide compound without using N,N-dimethylformamide while preventing the mixing of used solvent into waste water to reduce the waste water disposal load. SOLUTION: This benzyl(difluoromethyl) sulfide compound expressed by formula (4) (R is hydrogen atom, an alkyl, or the like; and (n) is 1-5) is produced by reacting a benzyl mercaptan metal salt expressed by formula (1) (R and n are same as those defined above; X1 is an alkali metal or an alkaline earth metal; and (m) is 1 when X1 is an alkali metal and is 2 when X1 is an alkaline earth metal) with a halogenated difluoromethane expressed by formula (2) (X2 is a halogen atom) in a binary layer system composed of a water phase and an organic phase.
